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The highly stereoselective conjugate addition of lithium (αR)-(α-methylbenzyl)allylamide 3 to (E)-tert-butyl penta-2,4-dienoate 4, followed by a stereoselective aldol reaction with acetaldehyde, are the key steps in the synthesis of the known β-lactam intermediate, (3S,4R)-3-E(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-vinylazetidin-2-one 2, for elaboration to thienamycin and its derivatives.

Original publication

DOI

10.1039/a700216e

Type

Journal article

Journal

Chemical Communications

Publication Date

01/01/1997

Pages

565 - 566